3,5-双(4-羧基苯基)碘苯 | 918410-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-双(4-羧基苯基)碘苯
• 中文别名: 4-N-BOC-氨基环己酮
• 英文名称: 1,3-bis(4-carboxyphenyl)-5-iodobenzene
• 英文别名: 3,5-bis(4-carboxyphenyl)-1-iodobenzene；3,5-bis(4-carboxyphenyl)iodobenzene；4-[3-(4-Carboxyphenyl)-5-iodophenyl]benzoic acid
• CAS: 918410-53-4
• 化学式: C₂₀H₁₃IO₄
• 分子量: 444.225
• InChiKey: HZEBIPAVTIVQDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-双(4-羧基苯基)碘苯 、 anthracene-2,6-diboronic acid 在 palladium diacetate potassium carbonate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 18.0h， 以65%的产率得到
  参考文献：
  名称：

  A cyclodextrin-insulated anthracene rotaxane with enhanced fluorescence and photostability

  摘要：

  我们合成了一种 β-环糊精蒽旋烷，发现其抗荧光淬灭和光漂白的能力明显强于未绝缘的蒽衍生物。

  DOI：

  10.1039/b700868f
• 作为产物：
  描述：

  1,3,5-三溴苯 在 四(三苯基膦)钯 正丁基锂 、 一氯化碘 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 3,5-双(4-羧基苯基)碘苯
  参考文献：
  名称：

  Homo- and Hetero-[3]Rotaxanes with Two π-Systems Clasped in a Single Macrocycle

  摘要：

  Here we present the first synthesis of a [3]rotaxane with two dumbbell components threaded through a single gamma-cyclodextrin macrocycle. This synthesis is carried out in two steps: first one dumbbell is synthesized threaded through the macrocycle to give a [2]rotaxane, then a second dumbbell is synthesized through the remaining cavity of the [2]rotaxane. We have synthesized a hetero- [3]rotaxane with one stilbene and one cyanine dye threaded through gamma-cyclodextrin, which exhibits quantitative energy transfer between the two encapsulated dyes. The stilbene [2]rotaxane intermediate in this synthesis has a remarkably high affinity for suitably shaped hydrophobic guests in aqueous solution, facilitating the synthesis of [3]rotaxanes and suggesting possible applications in sensors.

  DOI：

  10.1021/ja0665139

文献信息

• MOF Crystal Chemistry Paving the Way to Gas Storage Needs: Aluminum-Based <b>soc</b>-MOF for CH₄, O₂, and CO₂ Storage
  作者：Dalal Alezi、Youssef Belmabkhout、Mikhail Suyetin、Prashant M. Bhatt、Łukasz J. Weseliński、Vera Solovyeva、Karim Adil、Ioannis Spanopoulos、Pantelis N. Trikalitis、Abdul-Hamid Emwas、Mohamed Eddaoudi

  DOI：10.1021/jacs.5b07053

  日期：2015.10.21

  Al-soc-MOF-1 linker resulted in a noticeable enhancement in the working volumetric capacity at specific temperatures and pressures with amply conserved gravimetric uptake/working capacity. In contrast, further expansion of the organic linker (branches and/or core) led to isostructural Al-soc-MOFs with enhanced gravimetric uptake but noticeably lower volumetric capacity. The collective experimental and simulation

  有效地采用分子构建块方法构建了一系列具有SOC拓扑结构的新型等网状、高度多孔和稳定的铝基金属有机框架。从这个平台上，通过实验分离并充分表征了三种化合物：即母体 Al-soc-MOF-1 及其萘和蒽类似物。Al-soc-MOF-1 表现出出色的重力甲烷吸收（总容量和工作容量）。首次通过实验表明，Al-soc-MOF 平台可以解决能源部对 0.5 g/g（重量）和 264 cm(3) (STP)/cm(3) 具有挑战性的双重目标（体积）甲烷储存。此外，在所有微孔 MOF 中，Al-soc-MOF 在相对高压下表现出最高的二氧化碳总重量和体积吸收量以及最大的氧气总吸收量和可输送量。为了将 MOF 孔结构和功能与储气性能相关联，更好地理解结构-性能关系，我们进行了分子模拟研究，并使用不同的有机连接体评估了 Al-soc-MOF 平台的甲烷存储性能。发现缩短母体 Al-soc-MOF-1 接头导致在
• Influence of cyclodextrin size on fluorescence quenching in conjugated polyrotaxanes by methyl viologen in aqueous solution
  作者：Francine E. Oddy、Sergio Brovelli、Matthew T. Stone、Eric J. F. Klotz、Franco Cacialli、Harry L. Anderson

  DOI：10.1039/b821950h

  日期：——

  Poly(4,4′-diphenylenevinylene) rotaxanes and [2]rotaxanes with α-, β-, γ-cyclodextrin macrocycles were synthesised and their sensitivities to fluorescence quenching by methyl viologen in aqueous solution were determined, relative to uninsulated analogues. Stern–Volmer analysis revealed that the fluorescence quenching response of polyrotaxanes is strongly dependent on the diameter of the cyclodextrins. Polyrotaxanes, composed of the smaller diameter α- or β-cyclodextrins, are the least easily quenched, with Stern–Volmer constants about two orders of magnitude smaller than from the wider γ-cyclodextrin polyrotaxane and the uninsulated polymer. Time-resolved photoluminescence results demonstrate the crucial role of interchain aggregation on the sensitivity to fluorescence quenchers. The materials with the highest Stern–Volmer constants exhibit the most biexponential photoluminescence decay, which is indicative of aggregation, and the emission spectra of solutions containing methyl viologen resemble the early-time emission spectra (0–3 ns after excitation) of the unquenched samples. The results show that the threaded α-cyclodextrin is effective in preventing aggregation, and in hindering fluorescence quenching, even when only a small fraction of the conjugated polymer is encapsulated. This conclusion is relevant to the application of these materials in optoelectonic devices, such as light-emitting diodes, where it is essential to prevent luminescence quenching without hindering charge transport.

  合成了具有 α-、β-、γ- 环糊精大环的聚(4,4′-二苯基乙烯)轮烷和[2]轮烷，并测定了它们相对于未绝缘类似物在水溶液中被甲基紫罗兰烯淬灭荧光的灵敏度。斯特恩-伏尔默分析表明，聚二十二烷的荧光淬灭响应与环糊精的直径密切相关。由直径较小的α-或β-环糊精组成的聚二十二烷最不容易淬灭，其斯特恩-沃尔默常数比直径较大的γ-环糊精聚二十二烷和未绝缘聚合物的斯特恩-沃尔默常数小两个数量级。时间分辨光致发光结果表明，链间聚集对荧光淬灭剂的敏感性起着至关重要的作用。具有最高斯特恩-伏尔默常数的材料表现出最多的双指数光致发光衰减，这表明存在聚集现象，而含有甲基紫精的溶液的发射光谱与未淬灭样品的早期发射光谱（激发后 0-3 毫微秒）相似。结果表明，即使只封装了一小部分共轭聚合物，带螺纹的 α-环糊精也能有效防止聚集和阻碍荧光淬灭。这一结论与这些材料在发光二极管等光电设备中的应用有关，在这些设备中，必须在不妨碍电荷传输的情况下防止发光淬灭。
• A Conjugated Thiophene-Based Rotaxane: Synthesis, Spectroscopy, and Modeling
  作者：Leszek Zalewski、Michael Wykes、Sergio Brovelli、Massimo Bonini、Thomas Breiner、Marcel Kastler、Florian Dötz、David Beljonne、Harry L. Anderson、Franco Cacialli、Paolo Samorì

  DOI：10.1002/chem.200903353

  日期：2010.4.6

  A dithiophene rotaxane 1⊂β‐CD and its shape‐persistent corresponding dumbbell 1 were synthesized and fully characterized. 2D NOESY experiments, supported by molecular dynamics calculations, revealed a very mobile macrocycle (β‐CD). Steady‐state and time‐resolved photoluminescence experiments in solution were employed to elucidate the excited‐state dynamics for both systems and to explore the effect

  甲二噻吩轮烷1个⊂β-CD和其形状持久对应哑铃1合成并充分表征。由分子动力学计算支持的2D NOESY实验揭示了一个非常易移动的大环（β-CD）。溶液中的稳态和时间分辨光致发光实验用于阐明两个系统的激发态动力学，并探索环糊精包封的作用。发现1 ⊂β‐CD的光致发光（PL）光谱相对于哑铃1发生了蓝移（分别为2.81和2.78 eV）。另外，与先前的观察相反，当增加溶液的浓度或改变极性时，PL光谱以及带螺纹和无螺纹系统的衰减动力学均未显示变化，从而提供了缺乏无螺纹主链聚集趋势的证据。